Yellow azo dyes.



VIKTOR lfILLIG-ER AND ERNST FUSSENEGGER,. OF LUDWIG SHAFEN-ON-THE-RHINE,

GERMANY, ASSIG-NORS TO BADISCHE ANILIN & SODA FABRIK, 0F LUDWIGSHAFENON-THE-RHINE, GERMANY, A CORPORATION OF BADEN.

YnLLow AZO DYES.

No Drawing.

To all whom it may concern:

Be itknown that we, VIKTOR VILLIGER, Ph. D., and ERNST FUssnNEocnR, Ph.D., chemists, the first named a citizen of the Swiss Republic and thelatter a subject of the Emperor of Austria-Hungary, residing atLudwigshafen-on-the-Rhine, Germany, have invented new and usefulImprovements in Yellow Dyes, of which the following is a? specification.

Our invention relates to the manufacture of new azo coloring matterswhich are particularly suitable for use as pigments. We have discoveredthat by combining a diazotized chlorin derivative of ortho-nitranilinwith aceto-acetarylid, yellow coloring matters can be obtained which arecharacterized by their insolubility in water and oil and their fastnessagainst the action of light. They also possess the valuable property ofnot subliming. WVhen used in, the form of lakes, the possess brilliantgreenish yellow shades. ur'new coloring matters possess the furtherfollowing characteristics. They are insoluble in water and when reducedby means of zinc dust in the presence of an excess of hot alcoholicalkali they give rise to a non-diazotizable acid which melts at aboutfrom 207-209 C. The coloring matter obtainable according to ourinvention from rt-chlor-Qmitranilin and aceto-aeetani lid melts at about246 C., and that obtainable from 5-chlor-2 nitranilin andacetoacetanilid melts at about 236 C. As instances of aceto-acetarylidswhich can be employed according to our invention, we mentionaceto-acetanilid, aceto-acetortho-tolui- (lid, andaceto'acetpara-toluidid.

The following example will serve to illustrate further the nature of ourinvention and how it can be carried into practical effect, but ourinvention is not confined to this ex ample. The parts are by weight.Diazotize in the usual manner seventeen and threetenth parts of4-chlor-2-nitranilin and al- Specification of Letters Patent.

Application filed August 6, 1910. Serial No. 575,982.

Patented Apr. 18, 1911.

low the diazo solution to flow, while well stirring, into an aqueoussolution of seventeen and seven-tenths parts of aceto-acetanilid, towhich the necessary quantity of sodium acetate has been added. When thecombination is complete, filter off the coloring matter, wash it withwater, and either dry it or preserve it in the form of paste. In asimilar manner thecorresponding coloring matter can be obtained from'5-chlor-2- nitranilin.

Now what we claim is 1. As new articles of manufacture the azo coloringmatters which can be obtained by combining a diazotized chlorinderivative of ortho-nitranilin with an aceto-acetarylid, which coloringmatters possess yellowish colors, are insoluble in water, are fastagainst the action of light, and upon reduction with zinc dust in thepresence of an excess of hot alcoholic alkali yield an undiazotizableacid which melts at about from two hundred and seven to two hundred andnine degrees centigrade.

-2. As a new article of manufacture the azo coloring matter which can beobtained by combining diazotized 4-chlor-2-nitranilin withaceto-acetanilid, which coloring matter possesses a greenish yellowcolor, which is insoluble in water, is fast against the action of light,melts at'about two hundred and forty-six degrees centigrade and uponreduction with zinc dust in the presence of an excess of hot alcoholicalkali yields an undiazotizable acid which me] at about from two hundredand seven to two hundred and v nine degrees centigrade.

In testimony whereof we have hereunto set our hands in the presence oftwo subscribing witnesses. I

VIKTOR VILLIGER. I ERNST F USSENEGGER. Witnesses:

J. ALnc. LLOYD, ERNs'r L. Ivns.

